See How a Winnetka Couple Transformed Their Yard Into a Stunning Outdoor Living Space

When summers are as short as they are in the Midwest, it’s important to make the most of them. It was in that spirit that Winnetka residents Jared and Christy Vegosen hired Chalet Landscape, Nursery & Garden Center (Make It Better’s Best of 2018 Best Landscaper winner) to create a luxurious spot for alfresco dining, hosting parties, and spending time with their two young daughters. “Jared grew up in a city co-op without even a balcony, so he really wanted to have a nice outdoor space,” Christy explains.

Working with designer Sara Marcucci, landscape designer Robert Milani replaced the original jumbo horseshoe-shaped driveway in front with a discrete motor court that better fit the home’s Tudor character. A new brick garden wall with bullnose limestone detailing screens the view of the vehicles from the front door. “Extending the walls into the landscape creates a seamless connection between the architecture and the landscaping,” Milani says.

Lush gardens in front hint at the beauty in back.

The driveway pavers extend to the patio, making for a seamless transition from front to back.

The connection between the front and back yard is equally cohesive, thanks to a thermal bluestone path flanked by European-style columnar trees. In back, a large and handsome pergola, which was designed in Italy, built in Texas, and shipped to the site in pieces, creates a relaxing area to converse with friends.

A large pergola divides the patio into distinctive spaces.

A chandelier turns the cocktail area into an outdoor living room.

With the touch of a button, an awning extends and screens lower into place, protecting the occupants from rain and the inevitable mosquitoes. “If it’s over 45 degrees, you can sit there comfortably, even with the screens open,” Christy explains, pointing to the heat lamp in the ceiling.

The luxurious outdoor room is located conveniently next to the brick and stainless steel outdoor grill and a long zinc-topped dining table surrounded by tailored slipcovered chairs. Attention to detail is everywhere: There’s additional seating at a game table in front of the fireplace, which has been outfitted with a rustic arbor stained gray to match the pergola. Custom herb planters and bronze planters hand-forged in Detroit contain colorful flowers that complement the foliage surrounding the patio.

Outdoor slipcovers on the dining chairs make cleanup a breeze.

“It creates a nice vista from the patio looking out,” Milani says. “The dramatic drifts of perennial and annual pastel flower colors, spring bulbs, and leaf textures are on display from early spring to late fall.”

The view is about to become even more dramatic. Milani is putting the final touches on the design of a new swimming pool that will be installed later this summer. Centered with the pergola on the edge of the yard, the long, narrow pool will have a black bottom and a raised spa with a cascading edge. “It’ll be nestled into a bed of shrubs and perennials, so it’ll look like it’s part of the landscape,” Milani explains.

Soon, this view will include a pool.

Already the scene for charity events, garden walks, and many gatherings of family and friends, the updated outdoor entertainment space has far exceeded the owners’ expectations. “We have other families over all the time, so there are always lots of kids in the yard,” Christy says. And Jared is especially thrilled to finally have his own backyard entertaining space: “When he gets home, he heads right outside. We have a lot of fun out there.”